Heterocyclic compounds

Abstract

Compounds of the formula <IMAGE> wherein Het is <IMAGE> <IMAGE> +TR <IMAGE> n is an integer from 1 to 4, inclusive, preferably 2 or 3, R1 is H or acyl, R2 is H, R1O, -NHSO2R7, -NHCOR8, -NHCONHR8, -NH-CH2-C6H4-R9, -CH2OH, -CH2SO2R7, -CONHR8, halogen or -CN, R3 is H, halogen, R7 or -OR7, R2 and R3 together with each other are <IMAGE> R4 is H, -CH3 or -C2H5, R5 and R6 are each H or -CH3, R7 is C1-C4 alkyl, R8 is H or C1-C4 alkyl, R9 is H, C1-C4 alkyl or C1-C4 alkoxy optionally interrupted by oxygen, R10 and R12 are each H, CH3, Cl or OCH3, or together methylenedioxy, X is <IMAGE> or N, and Z is -CH2 or -CO; in the form of racemates, enantiomers, diastereoisomeric antipode pairs, and non-toxic, pharmacologically acceptable acid addition salts thereof. The compounds as well as the salts are useful as bronchospasmolytics, spasmolytics, muscle-relaxants, antiallergics and hypotensives.

We claim: 
     
       1. A compound of the formula ##STR105## wherein n is an integer from 1 to 4, inclusive; R 1  is hydrogen or carboxylic acid acyl;   R 2  is hydrogen, --OR 1 , --NHSO 2  R 7 , --NHCOR 8  --NHCONHR 8 , --NH--CH 2  --C 6  H 4  --R 9 , --CH 2  OH, --CH 2  SO 2  R 7 , --CONHR 8 , halogen or --CN;   R 3  is hydrogen, halogen, --R 7  or --OR 7  ;   R 4  is hydrogen, methyl or ethyl;   R 5  and R 6  are each hydrogen or methyl;   R 7  is alkyl of 1 to 4 carbon atoms;   R 8  is hydrogen or alkyl of 1 to 4 carbon atoms;   R 9  is hydrogen, alkyl of 1 to 4 carbon atoms or alkoxy of 1 to 4 carbon atoms, optionally interrupted by oxygen;   R 10  is hydrogen, alkyl of 1 to 4 carbon atoms, phenyl or pyridyl; and   Z is --CH 2  -- or --CO--; or a non-toxic, pharmacologically acceptable acid addition salt thereof.     
     
     
       2. A compound of claim 1, where   n is an integer from 1 to 4, inclusive;   R 1  is hydrogen;   R 2  is hydrogen, hydroxyl, --NHSO 2  CH 3 , --NHCOR 8 , --NHCONHR 8 , --NH--CH 2  --C 6  H 4  --R 9 , --CH 2  OH, --CH 2  SO 2  CH 3 , --CONHR 8 , chlorine or fluorine;   R 3  is hydrogen, chlorine, methyl or methoxy;   R 5 , R 6 , R 8  and R 10  are each hydrogen or methyl;   R 9  is hydrogen or 4-methoxy; and   Z is --CO--; or a non-toxic, pharmacologically acceptable acid addition salt thereof.     
     
     
       3. A compound of claim 1, wherein n is 2 or 3. 
     
     
       4. A compound of claim 2, wherein n is 2 or 3. 
     
     
       5. A broncholytic, uterus-relaxing or antiallergic pharmaceutical dosage unit composition consisting essentially of an inert pharmaceutical carrier and an effective broncholytic, uterus-relaxing or antiallergic amount of a compound of claim 1 where R 2  is other than --CONHR 8 . 
     
     
       6. The method of relieving bronchial spasms, relaxing the uterus or suppressing allergic reactions in a warmblooded animal in need thereof, which comprises perorally, parenterally or rectally administering to said animal an effective broncholytic, uterus-relaxing or antiallergic amount of a compound of claim 1 where R 2  is other than --CONHR 8 .